A synthetic route to 4-alkyl-?-methylhydrocinnamylaldehydes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F17%3A43913218" target="_blank" >RIV/60461373:22310/17:43913218 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s11164-016-2782-6" target="_blank" >http://dx.doi.org/10.1007/s11164-016-2782-6</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11164-016-2782-6" target="_blank" >10.1007/s11164-016-2782-6</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A synthetic route to 4-alkyl-?-methylhydrocinnamylaldehydes

Popis výsledku v původním jazyce

The 4-Alkyl-a-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-a-methylcinnamylaldehydes preparation with similar results. In the second step?hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.

Název v anglickém jazyce

A synthetic route to 4-alkyl-?-methylhydrocinnamylaldehydes

Popis výsledku anglicky

The 4-Alkyl-a-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-a-methylcinnamylaldehydes preparation with similar results. In the second step?hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Research on Chemical Intermediates

ISSN

0922-6168

e-ISSN

—

Svazek periodika

43

Číslo periodika v rámci svazku

neuveden

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

11

Strana od-do

2603-2613

Kód UT WoS článku

000398183900039

EID výsledku v databázi Scopus

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